CHESTER, Pa. – As Jay Sugarman tried to make a point about the benefits of forward thinking Thursday, he picked an unfortunate anachronism as his example.

“I always talk about this Waterloo example where we should not line up with our muskets and our men against their muskets and their men and see who wins,” said the Philadelphia Union’s majority owner. “If you’re going to play on their terms, you’re going to have a hard time beating them.”

Too often, Union games have felt not like a question of different types of muskets, but rather a Union team armed with mere slingshots sent out to the battlefield.

Much of Sugarman’s conversation Thursday – including time spent exclusively with The Athletic – upon the unveiling of Ernst Tanner as the club’s new sporting director struck the forward-facing tone that the owner sought. But Sugarman remains a recessed figure in the Union’s universe, rarely stepping into public view. Fans and outside...